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This qualitative multi-site case study explored how principals in four low-performing, highly diverse urban schools manage their daily administrative tasks while developing and sustaining trusting relationships with teachers to positively impact teacher retention. The study sought to understand how novice and experienced teachers felt about their relationships with their principal and how that influenced their decision to stay or leave. Data were collected through interviews, focus groups and document review. The study found that differentiated administrative support motivated experienced teachers to grow professionally and helped novice teachers with immediate problem-solving. When principals intentionally prioritized their time to develop trusting relationships with teachers, teachers’ decisions to stay was positively impacted which, in turn, can have a positive impact on student achievement.